CS232346B1 - 3,9-(7,15-diazadispiro[5,1,5,3]hexadekár»·16 yS)-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5]undekón a spósob jeho prípravv - Google Patents
3,9-(7,15-diazadispiro[5,1,5,3]hexadekár»·16 yS)-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5]undekón a spósob jeho prípravv Download PDFInfo
- Publication number
- CS232346B1 CS232346B1 CS834698A CS469883A CS232346B1 CS 232346 B1 CS232346 B1 CS 232346B1 CS 834698 A CS834698 A CS 834698A CS 469883 A CS469883 A CS 469883A CS 232346 B1 CS232346 B1 CS 232346B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- diphosphaspiro
- tetraoxa
- diazadispiro
- hexadecan
- formula
- Prior art date
Links
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 title claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- -1 hexadecan-15-yl Chemical group 0.000 claims description 2
- OLZALNPHLPDXMK-UHFFFAOYSA-N dispiro[5.1.5^{8}.3^{6}]hexadecane Chemical compound C1CCCCC21CC1(CCCCC1)CCC2 OLZALNPHLPDXMK-UHFFFAOYSA-N 0.000 claims 1
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZOSPIRSWAQIPSU-UHFFFAOYSA-N 7,15-diazadispiro[5.1.5^{8}.3^{6}]hexadecane Chemical compound C1CCCCC21NC1(CCCCC1)CNC2 ZOSPIRSWAQIPSU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000002301 combined effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
232346 2
Vynález sa týká 3,9-(7,15-diezadispiro[5,1,5,3]hexadekán-15-yl)-2,4,8,10-tetraoxa-3,9--diřosfaspiro [5,5]undekár;u a spdsobu jeho přípravy.
Stéricky bráněné aminy sú vysokoúčinné světelné stabilizátory polymérov. Fosfitypatria v sdčasnosti madzi významné druhy antioxidantov. Stéricky bráněné aminy inhibujdradikálové procesy, ktoré prebiehajú pri fotooxidácii polymérov a fosfity pSsobia pritermooxidácii polymérov ako rozkladaSe peroxidov. Nevýhodou nízkomolekulových zliíčenínstéricky bráněných piperidínov je ich značná prchavosť a vypieratel’nosť.
Uvedené nevýhody tento vynález odstraňuje. Podstatou vynálezu je 3,9(7,15-diazadispi-ro [5,1,5,3] hexadekán-15-yl)-? ,4,8,10-3,9~tetraoxa-3,9-difosfaspiro[5,5]undekán vzorca 1 Π
HN
P-'N
NH /1/
Podstatou vynálezu je áalej spSsob přípravy zlúčeniny vzorca I, ktorý sa vyznačuje tým,že sa na 7,15-diazadispiro[5,1 ,5,3]hexadekán vzorca II
H /11/
pčsobí 3,9-dichlór-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5] undekánom vzorca III Λγ-Ο\
Cl~p\ Λ /P_CI /m/ o—' '—o v pomere 2:1 v suchom dimetylformamide, alebo v suchom benzéne alebo toluéne v přítomnostitrietylamínu. Výhodou uvedeného vynálezu je jednak zvačáenie molekulovej hmotnosti stabilizátorea jednak příprava stabilizátore polymérov s kombinovaným účinkom, ktorý spája výhodnévlastnosti světelných stabilizátorov typu stéricky bráněných amínov a fosfitovýeh anti-oxidantov. Příklad 1 K roztoku 2,22 g (0,01 mol) 7,15-diazadispiro[5,1,5,3] hexadekánu v 20 ml suchéhodlmetylformamidu sa pri teplote okolo 20 °G za stálého miečania pomaly prikvapkáva roztok1,265 g (0,005 mol) 3,9-dlčhlór-2,4,8,10-tetraoxa-3,9-dlfosfaspiro[5,5] undekánu v 15 mlsuchého dlmetylformamidu. Zmes sa áalej mieša 5 h, potom sa vleje do 60 ml vody a silnézalkalizuje 4056 roztoku hydroxidu sodného. Vyextrahuje sa trikrát, chloroformem spojenéextrakty sa vysušia bezvodým síranom sodným e^ozpúšťadlo sa odpaří. Zostávajúci tuhý podielsa prekryštalizuje z etanolu. Získá sa produkt v podobě bielej kryStalickej látky s teplo-tou topenia v rozmedzí 129 až 132 °C.
Elementárna analýza pře C33H58N4°4P2
Vypočítané: C = 62,24 56 H = 9,18 56 N = 8,80 56 Nájdené: C = 62,32 56 H = 9,10 56 N = 8,72 %
Claims (2)
- /1/
- 2. SpSsob přípravy zlúčeniny podl’a bodu 1, vzorca 1, tým, že sa na 7,15~diaza dispiro[5,1 ,5,3] hexadekán vzorca II H NH ,'11/ pSsobí 3,9-diohlór-2,4,8,10-tetraoxa-3,9-difosfaspiroj5,5]undekánoin vzorca III 0^-0 Q—' '-—O P-CI v pomere 2:1 v suchom dimetylformamide, alebo v suchom benzéne alebo toluéne v přítomnostitrietylamínu. /111/
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS834698A CS232346B1 (cs) | 1983-06-24 | 1983-06-24 | 3,9-(7,15-diazadispiro[5,1,5,3]hexadekár»·16 yS)-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5]undekón a spósob jeho prípravv |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS834698A CS232346B1 (cs) | 1983-06-24 | 1983-06-24 | 3,9-(7,15-diazadispiro[5,1,5,3]hexadekár»·16 yS)-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5]undekón a spósob jeho prípravv |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS469883A1 CS469883A1 (en) | 1984-06-18 |
| CS232346B1 true CS232346B1 (cs) | 1985-01-16 |
Family
ID=5390332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS834698A CS232346B1 (cs) | 1983-06-24 | 1983-06-24 | 3,9-(7,15-diazadispiro[5,1,5,3]hexadekár»·16 yS)-2,4,8,10-tetraoxa-3,9-difosfaspiro[5,5]undekón a spósob jeho prípravv |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS232346B1 (cs) |
-
1983
- 1983-06-24 CS CS834698A patent/CS232346B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS469883A1 (en) | 1984-06-18 |
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